Bernie Sanders is a liberal standard-bearer on nearly every single policy issue, from climate change to taxation to financial regulation. But there’s one notable exception – guns.

With President Barack Obama and Hillary Clinton calling for a gut check on gun violence in America after the mass shooting at a historic black church in Charleston, S.C., the Vermont senator’s awkward history with the issue of gun control now seems poised to resurface.

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Arguably, the independent senator from Vermont has taken a pragmatic approach – his state prides itself on a deep hunting and gun culture and has traditionally fiercely defended its lax guns laws.

But while his campaign manager says he is “very moderate” on the issue, others call him “erratic.” To wit, he has voted against the Brady Bill, voted for an assault weapons ban, voted to allow firearms on Amtrak, and voted for universal background checks — upsetting gun-control and gun-rights advocates alike.

It’s not clear if his approach on the subject will hurt Sanders, who is enjoying a surge in the polls and overflow crowds on the campaign trail.

Still, as the gun-control conversation ratchets back up in the wake of the Wednesday’s shooting, Sanders risks looking like he’s out-of-touch with his progressive base and a bit tone deaf.

Sanders didn’t ignore the tragedy in Charleston, though there was an uncomfortable moment when his rally outside the Capitol for bolstering union retiree benefits overlapped briefly with a prayer vigil nearby for the victims of the shooting at the historically black church.

He canceled a campaign event for this Sunday in South Carolina and urged supporters in an email to make a contribution to the Emanuel AME Church with a link to the church’s website. He also issued a statement saying, “The Charleston church killings are a tragic reminder of the ugly stain of racism that still taints our nation.”

The statement did not mention guns, and when asked for further comment, Sanders’ campaign manager Jeff Weaver offered a less-than-forceful call for addressing the issue of gun violence: “This sick and tragic attack is an example of why we need to ensure that guns do not end up in the hands of dangerous people. We also ask ourselves how we rid our country of the repugnant racist views which apparently fueled this killer’s depraved act against our fellow Americans while they were in the sanctuary of a house of God.”

Clinton, the Democratic front-runner, delivered a more direct call to action during a speech in Las Vegas. “We have to face hard truths about race, violence, guns and divisions,” she said. She asked, “How many people do we need to see cut down before we act?”

Sanders’ history with gun control issues dates back to the very beginning of his Washington career.

Sanders, the legend goes, came to Congress because of the National Rifle Association. It’s not quite as simple as that — Vermonters remember Republican Peter Smith, who lost in the 1990 rematch after beating Sanders in 1988, as an awkward candidate poorly-suited for politics.

But after Smith came out in support of an assault-weapons ban after opposing it in his successful 1988 campaign against Sanders, the NRA invested heavily in defeating him — an opposition campaign that likened Smith to Pinocchio for his flip-flop and featured bumper stickers: “Smith and Wesson — Yes, Smith in Congress — No.”

The NRA didn’t campaign for Sanders in 1990, and Jeff Weaver, the campaign manager for his presidential bid and a longtime adviser, noted that Sanders supported an assault weapons ban and never embraced a pro-gun message.

“The easy position would have been to be against the assault weapons ban,” said Weaver, pushing back on the idea that Sanders catered to the NRA for political purposes. (Weaver made the comments before the Charleston shooting.)

Still, people recall that Sanders, then the four-term mayor of Burlington, was cautious not to step in. “Bernie let the NRA do his dirty work on that one to sink Smith. He played it very close to the vest,” said Garrison Nelson, a professor at University of Vermont who has known Sanders for around four decades.

Instead, Sanders said that he didn’t support the proposed Brady Bill, which instituted federal background checks and a five-day waiting period, and vowed that he wouldn’t flip-flop on the issue. He won the election by nearly 20 points.

Sanders’ improbable political journey — from quixotic left-wing politician scoring in the low single-digits in statewide elections to the longest-serving independent in congressional history — is one marked by this political acumen.

“The thing about Bernie which is different from most socialists, is Bernie wants to win,” Nelson said.

While in Congress, Sanders continued to oppose the Brady Bill because of the waiting period, which he said should be determined at the state level. He voted against the bill but in favor of an amendment from then-West Virginia Democratic Rep. Harley Staggers for an instant background check for all handgun purchases.

Still, his opposition to the landmark legislation prompted backlash, including a 1991 headline from the Vermont Times: “Who’s Afraid of the NRA? Vermont’s Congressmen, That’s Who,” featuring a photo of Sanders.

In the article, a Sanders adviser argued that a majority of Vermonters opposed the Brady Bill. That appeal to his constituents, some said, is an example of Sanders’ outreach to rural voters, particularly those in areas such as the conservative Northeast Kingdom, which has given him support throughout his career.

“Bernie basically has been able to appeal to groups that no one assumed would support socialists,” said Nelson — including gun-rights supporters, police during his time in Burlington and veterans’ groups as a senator. (Sanders, as chairman of the Senate Veterans’ Affairs Committee, helped craft and pass a bipartisan, multi-billion dollar legislation to reform the Veterans Affairs Department.)

Sanders’ vote against the Brady Bill was one of several that appealed to the gun-rights community, including a 2007 vote that prohibited foreign or United Nations aid to be used for gun control and a 2009 vote to allow firearms on checked bags on Amtrak.

The most distressing vote for gun-control advocates is his 2005 vote in favor of the Protection of Lawful Commerce in Arms Act, an NRA-backed bill to disallow gun manufacturers from being sued for negligence when people commit crimes with their guns. A recent Slate article focusing on the vote called Sanders a “gun nut,” and activists say the bill provides a level of legal protection for the gun manufacturers unprecedented for any other industry.

“Any smart person had to realize how insidious that law was,” said Brady Campaign president Dan Gross, who said the vote was a big reason for why he described Sanders’ gun-control record as “erratic.”

Weaver defended the vote, saying that while Sanders wants to ban assault weapons, gun manufacturers shouldn’t be sued if their product works effectively. “I believe he would make the same vote” today, said Weaver.

And even when voting for significant gun control measures, Sanders has tempered his support. In 2013, he voted for universal background checks and an assault weapons ban — the recent landmark gun legislation in the wake of the Sandy Hook shooting – and expressed reservations about the impact.

“If you passed the strongest gun control legislation tomorrow, I don’t think it will have a profound effect on the tragedies we have seen,” he told Seven Days Vermont a month before the vote, adding that he was still on the fence about the assault weapons ban.

In his official statement following his vote for the legislation in April 2013, Sanders opened with a caveat: “Nobody believes that gun control by itself is going to end the horrors we have seen in Newtown, Conn., Aurora, Colo., Blacksburg, Va., Tucson, Ariz. and other American communities.”

And on liberal comedian Bill Maher’s television show last year, Sanders said mental health was “maybe the more important issue” than gun control. “We’ve got millions of folks walking the streets who are need of mental health and they can’t walk into a place and get it,” he said.

“This is the NRA talking point. I’m not saying it’s wrong, but I’m just saying, that’s what they say,” Maher responded.

He has also often expressed that different states have different gun cultures and many decisions on the issue should be made not at the federal level, but the state and local levels.

Asked about those statements, Gross said: “Clearly a guy running for president … He does not do the truth any favors when he seeks to walk those fine lines,” adding that Sanders is trying to have it “both ways.”

Weaver dismissed the idea that Sanders had a poll-tested message on guns, calling that a “fantasy” and saying his moderate approach is an “organic position.”

The NRA has largely turned on Sanders — his most recent grade from the group is a D- and he has received an F before.

And Ed Cutler, president of Gun Owners of Vermont, said gun-rights group in the state just don’t trust him. “We, in Vermont, consider him anti-gun,” he said.